Discover a selection of 87 vacation rentals in Chesapeake City, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $180 per night, and houses and cottages are popular options for a stay in Chesapeake City. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesapeake City

How many vacation rentals are available around Chesapeake City, MD?

Our 2021 property listings offer a large selection of 87 vacation rentals around Chesapeake City. From 34 house rentals to 2 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Chesapeake City?

Yes, of course. Vrbo has 34 Houses in Chesapeake City. Our other popular types of vacation rentals in Chesapeake City include:

  • Cottages: 2 rentals available
  • Condos/Apartments: 3 rentals available
  • Cabins: 2 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Chesapeake City?

Yes, you can select your preferred vacation rental with pool among our 51 vacation rentals with pool available in Chesapeake City. Please use our search bar to access the selection of vacation rentals available.